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Dichloromethane → 2-(6-Amino-pyridazin-3-yl)-benzofuran-5-ol

HRID 501048
ノート
印刷プレビュー

反応式

HRID 501048 の反応式
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[N:16]=[N:15][C:14]([NH2:17])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:18]=1.C(Cl)Cl.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>O>[NH2:17][C:14]1[N:15]=[N:16][C:11]([C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:18][C:7]=3[CH:8]=2)=[CH:12][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 250149286-(5-Methoxy-benzofuran-2-yl)-pyridazin-3-ylamine

生成物 1

HCID 250149332-(6-Amino-pyridazin-3-yl)-benzofuran-5-ol収率 25.1%

試薬・触媒・溶媒 1

HCID 962Water
溶媒

実験手順

6-(5-Methoxy-benzofuran-2-yl)-pyridazin-3-ylamine (0.14 mmol) was mixed with CH2Cl2 (3 mL) at 0° C. under argon atmosphere. BBr3 (1M in CH2Cl2, 1.0 mL) was added dropwise and the mixture was stirred for 2 h at rt. The mixture was hydrolysed with H2O followed by NaHCO3 (sat. aq.). The resulting mixture was extracted with EtOAc and the organic extracts were dried over Na2SO4. After filtration and evaporation of the solvent, the crude material was purified by preparative HPLC to afford the title compound as a yellow solid (8 mg). 1H NMR δ ppm 9.21 (s, 1 H) 7.74 (d, 1 H) 7.40 (d, 1 H) 7.27 (s, 1 H) 6.96 (d, 1 H) 6.86 (d, 1 H) 6.76 (dd, 1 H) 6.69 (s, 2 H); MS m/z 228 (M+H).

後処理

  1. extractionThe resulting mixture was extracted with EtOAc
  2. dry with materialthe organic extracts were dried over Na2SO4
  3. filtrationAfter filtration and evaporation of the solvent
  4. customthe crude material was purified by preparative HPLC

出典と根拠

ORDレコード
ord-d98b6499593c4850ae3db2df2b789eba
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07772256B2

反応ノート

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